(a) Write a detailed mechanism for the isomerization of -D-fructofuranose from the hydrolysis of sucrose into an...
Question:
(a) Write a detailed mechanism for the isomerization of β-D-fructofuranose from the hydrolysis of sucrose into an equilibrium mixture of the β-pyranose and β-furanose forms.
(b) Although fructose usually appears as a furanose when it is part of a polysaccharide, in the pure crystalline form, fructose adopts a β-pyranose structure. Draw β-D-fructopyranose in its most stable conformation. In water at 20°C, the equilibrium mixture contains about 68% β-dpyranose and 32% β-D-furanose.
(c) What is the free-energy difference between the pyranose and furanose forms at this temperature?
(d) Pure β-D-fructopyranose has [α]D20°C = -132. The equilibrium pyranose – furanose mixture has [α]D20°C = -92. Calculate [α]D20°C for pure β-dfructofuranose.
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Organic Chemistry structure and function
ISBN: 978-1429204941
6th edition
Authors: K. Peter C. Vollhardt, Neil E. Schore